Solution and solid-phase halogen and C–H hydrogen bonding to perrhenate

Massena, Casey J.; Riel, Asia Marie S.; Neuhaus, George Francis; Decato, Daniel A.; Berryman, Orion B.

doi:10.1039/c4cc09242b

Cited by 47 publications

(51 citation statements)

References 69 publications

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“…Shortly thereafter, Beer and co‐workers reported the first cationic variant, namely a bidentate bromoimidazoliophane receptor ( 11 , Figure ) . Although the targets of these studies were mostly halides, there is also a growing number of receptors that bind more complex anions …”

Section: Halogen Bondingmentioning

confidence: 99%

Halogen Bonding in Organic Synthesis and Organocatalysis

Bulfield

Huber

2016

Chemistry A European J

538

348

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Halogen bonding is a noncovalent interaction similar to hydrogen bonding, which is based on electrophilic halogen substituents. Hydrogen-bonding-based organocatalysis is a well-established strategy which has found numerous applications in recent years. In light of this, halogen bonding has recently been introduced as a key interaction for the design of activators or organocatalysts that is complementary to hydrogen bonding. This Concept features a discussion on the history and electronic origin of halogen bonding, summarizes all relevant examples of its application in organocatalysis, and provides an overview on the use of cationic or polyfluorinated halogen-bond donors in halide abstraction reactions or in the activation of neutral organic substrates.

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Section: Halogen Bondingmentioning

confidence: 99%

Halogen Bonding in Organic Synthesis and Organocatalysis

Bulfield

Huber

2016

Chemistry A European J

538

348

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“…Furthermore, alteration of the aryl moiety (e.g., inclusion of N-based heterocycles such as pyridine) has enabled applications in coordination chemistry, such as selective transition metal and small molecule complexation as well as fluorescence sensing. 18–21 Addition of simple synthetic handles to the arenes in these systems has allowed for substitution of chiral functional groups, yielding macrocycles capable of saccharide complexation as well as asymmetric catalysis and chiral recognition. 22,23 Of all of the benefits of using an arylethynyl foundation on which to build a receptor, the rigidity, and hence preorganization, they lend to the structure is particularly important.…”

Section: Introductionmentioning

confidence: 99%

Solid-State Examination of Conformationally Diverse Sulfonamide Receptors Based on Bis(2-anilinoethynyl)pyridine, -Bipyridine, and -Thiophene

Berryman

Johnson

Vonnegut

et al. 2015

Crystal Growth & Design

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Utilizing an induced-fit model and taking advantage of rotatable acetylenic C(sp)–C(sp2) bonds, we disclose the synthesis and solid-state structures of a series of conformationally diverse bis-sulfonamide arylethynyl receptors using either pyridine, 2,2′-bipyridine, or thiophene as the core aryl group. Whereas the bipyridine and thiophene structures do not appear to bind guests in the solid state, the pyridine receptors form 2 + 2 dimers with water molecules, two halides, or one of each, depending on the protonation state of the pyridine nitrogen atom. Isolation of a related bis-sulfonimide derivative demonstrates the importance of the sulfonamide N–H hydrogen bonds in dimer formation. The pyridine receptors form monomeric structures with larger guests such as BF4− or HSO4−, where the sulfonamide arms rotate to the side opposite the pyridine N atom.

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“…[5][6][7][8][9][10][11][12][13][14] In brief, halogen bonding (XB) is termed as a directional non-covalent attractive interaction between an electrophilic halogen atom and a Lewis base. Recently, halogen bonding was utilized for specific anion recognition, despite XB's diversified implementation towards molecular recognition, [16][17][18][19][20][21][22] crystal engineering, 13,23-26 non-covalent organo-catalysis, [27][28][29] anion transport 30,31 and interlocked molecule formation. The electron density distributions around these atoms are anisotropic in nature and thus an electropositive region exists in the extension of a halogen-carbon bond which is termed as s-hole.…”

mentioning

confidence: 99%